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From Support  to DevOps: A Guide to Finding and Interviewing for DevOps Roles

I’ve known a lot of people who transitioned from general Apple support gigs to fields like information security, software development, people management, and of course, per the name of this article, DevOps. Some also went off to be teachers or left the industry, but the skills obtained supporting Macs lend themselves well to automation, and specifically pipelining DevOps workflows. So much so that when the wonderful Mat X founded an Apple-centric conference, he called it MacDevOps (

I’ve had a lot of people in DevOps report to me. In my current gig, I do a lot of this work myself while working on code and doing whatever random thing I do (I’m actually making icon packs so our front end and apps match up right now - ‘cause we’re at that point where we need components). But I also like to take a little time to write here each day and given that we’re starting to think about what scaling the company looks like when we leave beta, and compliance is a thing, it’s time to start thinking about DevOps. But that got me to thinking if there’s anything to provide for my fellow admins thinking to make the journey from supporting device to supporting code.

Transitioning from a traditional support role into DevOps can be a fantastic career move. Leveraging learned problem-solving skills, customer focus, and understanding of IT operations makes traditional admins uniquely positioned to thrive in this collaborative, fast-paced environment. DevOps is not just a job title; it's a cultural shift that bridges the gap between development and operations, aiming for faster software delivery and higher quality. As a support professional, most admins will already possess valuable insights into system behavior, user needs, and troubleshooting - those are all critical aspects of DevOps. Those who have done plenty of shell and python scripting will also find those skills transition well, even if there’s a little imposter syndrome (there shouldn’t be). Many who are looking to interview will find that a service-oriented mentality is something that can be leaned into during the interview.

Capitalizing on the Support Skillset

Support experience translates into several DevOps strengths:

  • Problem-solving: Expertise in diagnosing and resolving complex issues is indispensable for identifying and fixing bugs in staging and production environments.

  • Customer Focus: Navigating user frustrations and expectations aligns perfectly with DevOps's emphasis on user-centric development. Product managers get frustrated that it takes a long time to run unit tests or about build times, developers get frustrated they can’t access something in production, etc.

  • Communication: Knowing how to communicate effectively with diverse stakeholders is a crucial skill for collaboration in DevOps teams (for any team, maybe - but especially with developers).

  • Adaptability: The ability to handle ever-changing situations and learn new technologies will be invaluable in the dynamic DevOps world, where it kinda’ seems like there’s some new tool every day, like a new GitOps app or a Google Cloud Function to handle this or a Jenkins option for that.

  • Compliance: Many in Apple engineering positions saw a time  when all of a sudden there were compliance checklists, security checklists, etc. Knowing why those got created and how to navigate them helps as much with DevOps as anything else.

DevOps is a fairly new field (like Mac support might have been in the early days). Not a lot of people have 10 years of experience. So being able to lean into, and articulate, past experiences that align well is a great way to get to the next stage of an interview process. Start on internal job boards, because it’s easier to transition inside a company, but then looking beyond that, consider a few specific titles.

Finding The Ideal DevOps Role

Keeping those strengths in mind, explore diverse DevOps roles that best match interests and experience:

  • Infrastructure Engineer: Focuses on maintaining and automating IT infrastructure, leveraging existing knowledge of troubleshooting and operational processes.

  • Release Engineer: Manages the release of software updates, capitalizing on an understanding of user impact and deployment procedures.

  • Security Engineer: Secures DevOps pipelines and applications, utilizing an already keen awareness of system vulnerabilities and best practices.

  • Site Reliability Engineer (SRE): Ensures application performance and reliability, aligning with  problem-solving abilities and operational insights.

Tailoring The Search and Applications

Actively network with DevOps professionals through online communities and events. Participate in open-source projects to gain practical experience and showcase your skills. When applying for roles, highlight relevant support experiences using the STAR method (Situation, Task, Action, Result) to demonstrate the ability to tackle challenges and deliver value. Emphasize an eagerness to learn new technologies and adapt to a collaborative environment (after all, there’s a reason support is going to be in the rear-view mirror).

Conquering DevOps Interviews

DevOps interviews typically blend technical assessments with behavioral and scenario-based questions. Here's how to shine:

  • Brush up on DevOps Fundamentals: Understand key concepts like CI/CD pipelines, configuration management tools, and infrastructure automation. Know the stack of a company (if the post says Jenkins and Artifactory or Xcode with GitHub or whatever, brush up on that specific stack - it’s surprising how easy it is to get half the knowledge but hard it is to get the other half).

  • Practice Coding Tests: Platforms like HackerRank and LeetCode offer practice problems relevant to DevOps roles.

  • Master Behavioral Questions: Prepare examples from past support experiences that showcase collaboration, problem-solving, and initiative. Again, lean into past experiences and soft skills that are really hard to teach.

  • Ask Insightful Questions: Demonstrate a genuine interest and research by preparing thoughtful questions about the company's DevOps practices and culture.

Also, it’s a new job so new pay bands. Research average salaries for the target role and location. Tools like Glassdoor make this incredibly easy. Use that support experience and any acquired DevOps skills to confidently negotiate a fair compensation package. Keep in mind that scripting an Active Directory bind is similar to scripting xcodebuild!

Landing the job is just the beginning. Continuously learn, contribute actively to the team, and embrace the collaborative DevOps culture - especially open source projects. Remember, transitioning from support to DevOps is a journey, not a destination. Embrace the challenges, leverage that unique skillset, and enjoy the time with Kubernetes, Ansible, Terraform, or whatever new stack of building blocks are there!

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